Packages
Private sailing charters for couples, families, and small groups
Sunset cruises along Long Island’s East End
Customized event charters, including weddings, anniversaries, and celebrations
Special seasonal packages, such as holiday sails or fireworks-viewing cruises
Pricing varies depending on duration, group size, and customization; we emphasize intimate, high-quality experiences rather than large tours.
2-Hour Classic Sail (Shared or Private)
Duration: 2 hours
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina
Capacity: Up to 6 guests (intimate, upscale experience)
Pricing: Weekday $800 per group | Weekend/Peak $900 per group
Notes: Prices are per group, not per person.
Step aboard Selina, a classic wooden sailing yacht, and experience the charm of traditional sailing on the waters of Shelter Island and the North Fork. Guests are welcome to participate in raising the sails and learning the rhythms of classic yacht sailing — or simply sit back, relax, and take in the scenery.
Highlights:
Hands-on sailing (optional)
Calm, scenic waters of Shelter Island & Peconic Bay
Historic wooden yacht experience
Bluetooth music connection for your personal playlist
Limited to 6 guests for a private-feeling sail
Optional Add-Ons
Charcuterie Board: $120
Premium Flower Arrangement: $175
Bottle of Bubbly (chilled onboard): $75
Professional Photographer 30 min: $350 | 60 min: $600
Custom Sail Message Setup: $80
Pre-loaded Bluetooth Playlist Assistance: $30
Romantic Champagne Sunset Sail
Duration: 2 hours (evening departures timed for golden hour & sunset)
Departure Locations: Greenport Village – Mitchell Park Marina OR Shelter Island – Dering Harbor
Capacity: Up to 6 guests
Pricing: Weekday $850 per group | Weekend/Peak $975 per group
Notes: Prices are per group, not per person.
Designed for romance and atmosphere, this sail pairs classic sailing with golden-hour light and sweeping waterfront views.
Included:
Champagne toast for each guest (non-alcoholic sparkling available)
Chilled still water
Cozy blankets for evening breezes
Cushioned seating
Bluetooth music connection for your personal playlist
Expert captain & crew sharing local maritime stories
BYOB
Bring your favorite North Fork wine or bubbly
Glassware, ice & water provided
Optional Add-Ons
Charcuterie Board: $120
Premium Flower Arrangement: $175
Bottle of Bubbly (chilled onboard): $75
Professional Photographer 30 min: $350 | 60 min: $600
Custom Sail Message Setup: $80
Pre-loaded Bluetooth Playlist Assistance: $30
Family Sailing Charter
Duration: Approximately 2 hours (longer sails available upon request)
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village
Capacity: Up to 6 guests
Pricing: Weekday $800 per group | Weekend/Peak $900 per group
Notes: Prices are per group, not per person.
A relaxed, family-friendly sailing experience designed for all ages.
Highlights:
All ages welcome
Infant, youth, and adult life jackets provided
Wildlife spotting (ospreys, fish, dolphins in season)
Optional hands-on sailing
Calm, scenic routes ideal for families
Bluetooth music connection for your personal playlist
BYOB
Bring snacks or your favorite beverages
Glassware, water provided
Optional Add-Ons: (same as above) + kids snack pack! $30
Half-Day Private Charter
Duration: 4 hours (customizable itinerary)
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village
Capacity: Up to 6 guests (private charter only)
Pricing: Weekday $1,250 per group | Weekend/Peak $1,350 per group
Notes: Prices are per group, not per person.
Enjoy an extended private sailing experience exploring the best of Shelter Island and the North Fork. Guests can anchor in quiet coves to swim, soak up the sun on the deck, and enjoy a picnic aboard. Don’t want to pack your own lunch? We can coordinate a curated picnic for you as an add-on.
Highlights:
Tour Dering Harbor, Greenport waterfront, Shelter Island coves & Peconic Bay
Flexible pace and route
Anchor, swim, sunbathe, and picnic on board
Private yacht experience
Bluetooth music connection for your personal playlist
BYOB & Dining
Bring your favorite North Fork wine and picnic lunch OR let us arrange it
Glassware, water & ice provided
Optional Add-Ons: (same as above)
Full-Day Private Charter
Duration: 8 hours (fully customizable)
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village
Capacity: Up to 6 guests (private charter only)
Pricing: Weekday $1,900 per group | Weekend/Peak $2,100 per group
Notes: Prices are per group, not per person.
The ultimate sailing day. Spend the day exploring Shelter Island, Greenport, and Peconic Bay, with plenty of opportunities to anchor, swim, soak up the sun, enjoy a picnic on board, and even circumnavigate Shelter Island if desired. Don’t want to pack your own lunch? We can coordinate a curated picnic for you as an add-on. We can also drop you off at a local restaurant in the area with prior coordination.
Highlights:
Explore Shelter Island coves, Greenport, and Peconic Bay
Swim, relax, and sail throughout the day
Tailored itinerary based on your preferences
Anchor, picnic, sunbathe on deck, and circumnavigate Shelter Island
Optional drop-off at a local restaurant (coordinated in advance)
Bluetooth music connection for your personal playlist
BYOB & Dining
Bring your own picnic lunch or let us handle arrangements
Glassware, water & ice provided
Optional Add-Ons: (same as above)
Private Engagement & Marriage Proposal Sail
Duration: 2 hours (longer sails available upon request)
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina
Pricing: Weekday $1,100 per group | Weekend/Peak $1,250 per group
Notes: Prices are per group, not per person.
Create an unforgettable proposal or intimate celebration.
Included:
Proposal coordination & hidden ring assistance
Crew-captured photos of the moment
Custom playlist via Bluetooth
Optional Add-Ons:
Local florist arrangements: $175
Charcuterie Board: $120
Professional Photographer 30 min: $350 | 60 min: $600
Bottle of Bubbly (chilled onboard): $75
Don’t see what you want listed? Inquire and we are happy to create a perfect, personalized, and special experience for you.
Moonrise Cruise
Duration: 2 hours
Season: May–August
Schedule: 7:30 PM – 9:30 PM
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina
Pricing: Weekday $850 per group | Weekend/Peak $975 per group
Notes: Prices are per group, not per person.
Options:
Shared sail (2+ guests) or private charter
Bluetooth music connection for your personal playlist
Included
Cozy blankets
Relaxed evening sailing
BYOB:
Bring wine or bubbly (glassware, water & ice provided)
Optional Add-Ons:
Local florist arrangements: $175
Charcuterie Board: $120
Professional Photographer 30 min: $350 | 60 min: $600
Bottle of Bubbly (chilled onboard): $75
Nautical Wedding Package
Starting at $2,800–$3,200 depending on guest count and add-ons
Notes: Prices per group/ceremony, not per person.
Celebrate your love in timeless style with a private waterfront wedding aboard Selina. Exchanging vows on a classic wooden yacht as the sun sets over Shelter Island and the Peconic Bay creates a truly unforgettable, intimate, and romantic setting.
Experience Includes:
Private Sailing Ceremony: Up to 6 guests, fully exclusive for you and your closest loved ones
Dockside Waterfront Option: Invite up to 12 guests from the deck or shoreline
Licensed NY Officiant included to make your ceremony seamless and stress-free
Tailored Romantic Atmosphere: Bluetooth music connection for your personal playlist, soft blankets, and the gentle sound of sails and water
Professional Photography & Capture Options: Keep memories forever with optional photographer add-on
Optional Add-Ons to Perfect Your Day:
Local florist arrangements & romantic floral decor: $175
Charcuterie Board or Champagne toast: $120–$175
Professional Photographer 30 min: $350 | 60 min: $600
Custom Sail Setup for proposals or vow enhancements: $80
Personalized Requests: Don’t see exactly what you want? We’ll happily design a bespoke romantic experience, from special flowers and lighting to custom surprises.
Private Sailing Lessons
Group Size: Up to 6 guests (private)
Season: May–September
Pricing: $225 per person (2 hr)
Group Minimum: $450 for 2 people
Notes: Prices are per person for lessons.
Learn to sail aboard a historic wooden yacht with hands-on instruction tailored to your experience level.
Skill Levels:
Beginners to intermediate sailors
Waters Sailed:
Peconic Bay
Shelter Island Sound
Topics Covered:
Helm control
Sail trim
Navigation basics
Seamanship fundamentals
Bluetooth music connection for your personal playlist
Optional Add-Ons:
Local florist arrangements: $175
Charcuterie Board: $120
Professional Photographer 30 min: $350 | 60 min: $600
Special Event Charters
Fourth of July Fireworks Charter (Private)
Duration: ~3–4 hours evening sail
Departure: Shelter Island – Dering Harbor or Greenport Village – Mitchell Park Marina
Capacity: Up to 6 guests
Pricing: $1,850 per group (Holiday peak $2,000)
Notes: Private sail | Prices per group | Sales tax & gratuity applied at checkout
Description:
Experience the Fourth of July like never before aboard Selina! Enjoy scenic sailing, festive atmosphere, and a front‑row water view of the spectacular fireworks display. This premium private charter is a highlight of the season and sells out every year — book early!
Included:
Priority positioning for fireworks viewing
Bluetooth music & commentary
Light snacks & chilled water aboard
Comfortable viewing deck and classic yacht ambiance
Optional Add‑Ons:
Sparkling toast package
Professional photographer
Charcuterie board
Custom sunset sail timing
Bachelorette Parties
Celebrate with a private, stylish sail tailored to your group’s vibe.
Optional Add-Ons: (same as above):
For this one I want to have it set up in FareHarbor but not activated because I don’t know which days are going to be slow
Public Ticketed Weekly Sail (2 Hours)
Duration: 2 hours
Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina
Pricing: Adult $95 | Youth (5–15) $65 | Infant (under 5) $25
Notes: Ticket sales are per person. Children under 5 sail free with an adult. Sales tax and gratuity applied at checkout. Seats are limited — book early!
Description:
Shared sailing experience on Selina
Scenic cruise around Shelter Island & Peconic Bay
Optional participation in raising sails
BYOB welcome (glassware & ice provided)
Bluetooth music connection for your personal playlist
Expert captain & crew sharing local maritime stories
